Cesium carbonate → HCID 178461250, compound

Participants

Reaction Conditions

Reaction Steps

4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (6.8 g, 22.8 mmol), 5-chloropyridine-3-boronic acid (3.95 g, 25.1 mmol), cesium carbonate (22.3 g, 68.4 mmol), and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride (1.67 g, 2.28 mmol) were combined in a vial that had been oven-dried and flushed with nitrogen. Dioxane (73 mL) and water (18 mL) were added, and the vial was sealed and heated to 90° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes, linear gradient) to afford 6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine. MS ESI calc'd. for C19H20Cl2N4 [M+H]+ 375. found 375.

Provenance & Evidence